To be incarcerated is to be deprived of the choices available to those in the free world. In the absence of those choices, carceral facilities dictate the ways that individuals may engage. If an incarcerated person wants to communicate with someone who is not in their facility, they have very limited options. Because of the extended erosion of attorney-client privilege, for years attorneys have identified in-person visitation as the only way to ensure attorney-client privilege is protected while they communicate with their incarcerated clients. When in-person visitation was eliminated due to COVID-19 lockdowns, every communication method that incarcerated individuals were able to access carried with it the likelihood or certainty of surveillance, destroying their access to communication with attorneys that preserved the privileged nature of such communication. Herein lies the essential attorney-client privilege issue laid bare by COVID-19: the state has incarcerated people, deprived them of communications protected by attorney-client privilege, and placed specific surveillance on every other meaningful and effective method people have to communicate with their attorney. These actions are even more damning in light of the multitude of individuals held in pretrial detention, many unable to pay bail, who then are restricted access to their own defense counsel, stealing their ability to participate in their own defense. Such deprivation runs contrary to the Sixth Amendment and is a direct illustration of why meaningful protections must be placed on communications between incarcerated individuals and their attorneys. What follows is a study of the four main alternative communication methods offered during COVID-19 lockdowns to incarcerated individuals: mail, phone, email, and video calls, and the ways in which each fail to afford communications actually protected by attorney-client privilege. This Comment then identifies how holistic and overarching reforms of communication systems for incarcerated individuals and their attorneys must be implemented in order to uphold attorney-client privilege and the criminal defendant’s Sixth Amendment constitutional right to counsel.